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TAMPA BAY • FEBRUARY 23-24 2026

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Good Boss, Bad Boss – Which One Are You?

Think about your work experiences before you became the boss. Like most, you probably had some good bosses and others who were not so great.

One of my worst bosses was a dangerous combination of personal ego and inept leadership. He claimed to hire people who were “self-starters” because he did not have time to micromanage. He wanted to be able to hand out projects, and then have them run smoothly without much more of his input.

Autonomy in the workplace is what most employees seek, but it can backfire on employers and employees alike. This particular boss always managed to step in and take a bow at the crucial moment when one of his employees was succeeding without any real oversight from him. He lost a key employee when the client saw through his act and hired the employee out from under him. That employee was no longer inclined to show loyalty to her original employer because he had taken credit for all of her hard work on a number of occasions.

Oddly enough, this incident did not force the boss to be more involved in the day-to-day operations. He was personally wounded by the loss of that employee, but he did not alter his management style. He did not even step up to fill the gap after losing his second-in-command.

Since he refused to give detailed instructions to his employees, when they weren’t clear on what to do next, they sat still. One such employee did nothing but surf social media and read news on the internet for several months after losing a major client. The boss knew this employee had no other client work to do, but he didn’t bother to assign anything else.

The employee became more disgruntled everyday because he had nothing to do and was not enough of a “self-starter” to ask for some productive work. Actually, I think he was waiting for the boss to trust him with another client, but the boss was oblivious to that. He just pretended to be busy while the boss paid his salary, on the backs of the other employees, for a couple months.

In part due to a rebellion from the rest of the staff, the boss was forced to fire this employee. It was too late, though. The boss had lost the trust of everyone in the office. The staff exited one by one faster than the boss could replace them, and clients were right behind them. The business eventually folded.

Sometimes it can be fun to tell old boss horror stories. That is, when the experience is far enough behind you that the sting is gone. That particular boss took me years to get over. I had another boss after that who was absolutely wonderful, but I could never truly trust him. In comparison he seemed too good to be true. Happily working away in my cubicle, I often swore I heard footsteps.

What About the Good Bosses?

In my career, good bosses were unfortunately out numbered by the bad ones, or so it seems. It might be that bad work experiences stick with you longer. That is a sad reality all by itself. Sometimes you don’t realize what a good boss you are working for until years later, in retrospect.

One such boss I had early in my career learned to be a manager by being managed. She didn’t tell me that, but I figured it out from the stories she told. She was not a college graduate, had never taken any business classes or management training, and didn’t use any fancy leadership jargon, although she was extremely well read.

This manager was passionate about the work. She took charge of her department because she wanted everyone’s work to be exemplary, not for bragging rights but because the work was important to her and she felt it should be done right. She defended her department to other, more senior, managers and fought for the resources needed to complete this important work.

This boss was a pleasure to work for. Although she kept close tabs on my workload and the quality of the work I produced, I never felt micromanaged. She listened, and guided, and taught, all while she continued to learn herself. And at the end of the day, when I walked past her office on my way out the door, she always thanked me for my work that day.

Experiences with managers like that fuel my belief that there are good bosses out there. My hope for mankind, is that there are really more good bosses than bad bosses. The only way to be sure that is true is to make more good bosses.

Born to Boss

Let’s skip the semantic discussion of the word boss and agree that for the purposes of this article, it is just a title. There is no attitude implied here. A boss can be a business owner, an employer, or a manager. When I use the word boss, I simply mean someone who is in charge of other people and their work.

In fact, when we are born, we spend a period of time going through a cognitive state in which we are the only object in the universe. This egotistic perspective, although natural, of course, is not conducive to effective management techniques.

When someone becomes a boss, he makes some decisions, whether conscious or unconscious. I advocate for making conscious decisions about how you want to manage your staff to reach your goals. What kind of boss do you want to be? How do you want your employees to perceive you?

You can probably come up with your own list from past experiences, but here are some qualities of a bad boss:

  • Too busy to speak with employees directly
  • Does not listen
  • Thinks he is the smartest guy in the room
  • Looks for mistakes
  • Does not manage his own time well
  • Sends employees to do tasks he wouldn’t do himself
  • Attempts to solve problems with ultimatums
  • Takes credit for employees’ work
  • Limits career growth of employees
  • Raises his voice or is in other ways disrespectful

These are obviously qualities to avoid when assuming your role as the boss. There may be circumstances under which you could justify behaving in one of these ways, but I assure you it will be the wrong choice. Under no conditions can you be a good boss and have any of these habits.

When otherwise good people and well-meaning bosses resort to any of this type of behavior, it is because they cannot think of an alternative. A problem presents itself and you do not have a ready solution, so you slip into defensive mode. Some of these behaviors are just reflexes, things we do automatically without thinking.

The antidote to bad boss behaviors is to think and make a conscious decision not to go that way. Instead, focus on these qualities of a good boss:

  • Elevates members of the team above himself
  • Encourages career growth and development
  • Listens
  • Considers his employees peers and equals
  • Respects his employee even when disappointed with their work
  • Connects with each team member on an individual level
  • Communicates information and expectations clearly
  • Supports his employees when things go wrong

Good bosses don’t know everything and are not perfect. They recognize when someone else has a better idea, and they know when to ask for help. They are humble and ask questions while holding employees accountable.

When assessing your qualities as a boss, remember what it was like to be an employee. Are you the kind of boss you would want to work for? Why or why not?

Not an ideal boss? Need some fresh, practical insights or a problem-solving partner? Contact me below to schedule a FREE Consultation!

Christine Andola
Christine Andola
Christine has mastered the art of human connection, working for more than 30 years in the communication and marketing field. In any setting, communication is all about the people, as this inquisitor of human behavior has discovered. An experienced writer, Christine’s work has been published in several regional and online magazines. She writes about food, health, business, and other topics. In her book, Who Knew? Lessons From My First 40 Years, Christine shares candid anecdotes and real-life lessons learned from years of complex family dynamics, awkward social missteps, marriage gone wrong, grief, and death. Christine is also a highly successful copywriter with experience developing copy and brand voice for companies across a wide array of industries. At heart, Christine is a native New Yorker who has lived in every region of the state, traveled the entire length of the Erie Canal by boat, and navigated both the St. Lawrence and the Hudson rivers.

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